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Showing NP-Card for Methoxyacetic acid (NP0136263)

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Record Information
Version2.0
Created at2022-05-12 15:10:00 UTC
Updated at2022-05-12 15:10:00 UTC
NP-MRD IDNP0136263
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethoxyacetic acid
DescriptionMethoxyacetic acid, also known as 2-methoxyacetate or CH3OCH2COOH, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Methoxyacetic acid was first documented in 2013 (PMID: 23290149). Methoxyacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 23290947) (PMID: 24798094) (PMID: 25606576) (PMID: 26001161).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136263 (Methoxyacetic acid)


  Mrv1652304062013062D          

  6  5  0  0  0  0            999 V2000
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
M  END
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3D MOL for NP0136263 (Methoxyacetic acid)

     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.8433    0.2194   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4901    0.5325   -0.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2939   -0.5716    0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7058   -0.1035    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716   -0.8790    0.5413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0603    1.2312    0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767   -0.1868    0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0539   -0.5660   -0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736    1.1552   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -1.0271    1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -1.3125   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1031    1.5081   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  6 12  1  0
M  END
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3D SDF for NP0136263 (Methoxyacetic acid)


  Mrv1652304062013062D          

  6  5  0  0  0  0            999 V2000
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O3/c1-6-2-3(4)5/h2H2,1H3,(H,4,5)

> <INCHI_KEY>
RMIODHQZRUFFFF-UHFFFAOYSA-N

> <FORMULA>
C3H6O3

> <MOLECULAR_WEIGHT>
90.0779

> <EXACT_MASS>
90.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.228962068512866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxyacetic acid

> <ALOGPS_LOGP>
-0.49

> <JCHEM_LOGP>
-0.39746725666666666

> <ALOGPS_LOGS>
0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.826714570822478

> <JCHEM_PKA_STRONGEST_BASIC>
-4.170962596718141

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
19.097099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methoxyacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0136263 (Methoxyacetic acid)

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PDB for NP0136263 (Methoxyacetic acid)
HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    6                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    2                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0136263 (Methoxyacetic acid)
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SMILES for NP0136263 (Methoxyacetic acid)
COCC(O)=O
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INCHI for NP0136263 (Methoxyacetic acid)
InChI=1S/C3H6O3/c1-6-2-3(4)5/h2H2,1H3,(H,4,5)
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View in JSmol
Synonyms
ValueSource
2-Methoxyacetic acidChEBI
CH3OCH2COOHChEBI
Methoxyethanoic acidChEBI
2-MethoxyacetateGenerator
MethoxyethanoateGenerator
MethoxyacetateGenerator
Methoxy-acetic acidHMDB
Methoxyacetic acid (acd/name 4.0)HMDB
Methoxyacetic acid, calcium saltHMDB
Methoxyacetic acid, sodium saltHMDB
Chemical FormulaC3H6O3
Average Mass90.0779 Da
Monoisotopic Mass90.03169 Da
IUPAC Name2-methoxyacetic acid
Traditional Namemethoxyacetic acid
CAS Registry NumberNot Available
SMILES
COCC(O)=O
InChI Identifier
InChI=1S/C3H6O3/c1-6-2-3(4)5/h2H2,1H3,(H,4,5)
InChI KeyRMIODHQZRUFFFF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassCarboxylic acids  
Direct ParentCarboxylic acids  
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.49ALOGPS
logP-0.4ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)3.83ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.1 m³·mol⁻¹ChemAxon
Polarizability8.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041929  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID11750  
KEGG Compound IDNot Available
BioCyc IDCPD-12993  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12251  
PDB IDNot Available
ChEBI ID132098  
Good Scents IDNot Available
References
General References
  1. Yang B, Sun H, Li W, Zhu C, Jian B, Hou W, Wang H, Yuan J, Yao B: Expression of Rap1 during germ cell development in the rat and its functional implications in 2-methoxyacetic acid-induced spermatocyte apoptosis. Urology. 2013 Mar;81(3):696.e1-8. doi: 10.1016/j.urology.2012.11.005. Epub 2013 Jan 3. [PubMed:23290149  ] 
  2. Fromme H, Nitschke L, Boehmer S, Kiranoglu M, Goen T: Exposure of German residents to ethylene and propylene glycol ethers in general and after cleaning scenarios. Chemosphere. 2013 Mar;90(11):2714-21. doi: 10.1016/j.chemosphere.2012.11.051. Epub 2013 Jan 3. [PubMed:23290947  ] 
  3. Dayan C, Hales BF: Effects of ethylene glycol monomethyl ether and its metabolite, 2-methoxyacetic acid, on organogenesis stage mouse limbs in vitro. Birth Defects Res B Dev Reprod Toxicol. 2014 Jun;101(3):254-61. doi: 10.1002/bdrb.21108. Epub 2014 May 2. [PubMed:24798094  ] 
  4. Parajuli KR, Zhang Q, Liu S, Patel NK, Lu H, Zeng SX, Wang G, Zhang C, You Z: Methoxyacetic acid suppresses prostate cancer cell growth by inducing growth arrest and apoptosis. Am J Clin Exp Urol. 2014 Dec 25;2(4):300-12. eCollection 2014. [PubMed:25606576  ] 
  5. Hlozek T, Bursova M, Coufal P, Cabala R: Identification and quantification of acidosis inducing metabolites in cases of alcohols intoxication by GC-MS for emergency toxicology. J Pharm Biomed Anal. 2015 Oct 10;114:16-21. doi: 10.1016/j.jpba.2015.04.039. Epub 2015 May 6. [PubMed:26001161  ]